Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis

Sandrine Ventre; Filip R. Petronijevic; David W.C. Macmillan

doi:10.1021/jacs.5b02244

Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis

Sandrine Ventre, Filip R. Petronijevic, David W.C. Macmillan

Chemistry

Research output: Contribution to journal › Article › peer-review

224 Scopus citations

Abstract

The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO₂-extrusion and F^• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

Original language	English (US)
Pages (from-to)	5654-5657
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	17
DOIs	https://doi.org/10.1021/jacs.5b02244
State	Published - May 6 2015

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/jacs.5b02244

Fingerprint Dive into the research topics of 'Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis'. Together they form a unique fingerprint.

Cite this

@article{30fae34fb2c24333bf4ffb941c472e60,

title = "Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis",

abstract = "The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.",

author = "Sandrine Ventre and Petronijevic, {Filip R.} and Macmillan, {David W.C.}",

year = "2015",

month = may,

day = "6",

doi = "10.1021/jacs.5b02244",

language = "English (US)",

volume = "137",

pages = "5654--5657",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis

AU - Ventre, Sandrine

AU - Petronijevic, Filip R.

AU - Macmillan, David W.C.

PY - 2015/5/6

Y1 - 2015/5/6

N2 - The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

AB - The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F• transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

UR - http://www.scopus.com/inward/record.url?scp=84928963782&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84928963782&partnerID=8YFLogxK

U2 - 10.1021/jacs.5b02244

DO - 10.1021/jacs.5b02244

M3 - Article

C2 - 25881929

AN - SCOPUS:84928963782

VL - 137

SP - 5654

EP - 5657

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 17

ER -